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RU2350609C2 - Benzofuran and benzothiophen derivatives applied for hyperproliferative disease treatment - Google Patents

Benzofuran and benzothiophen derivatives applied for hyperproliferative disease treatment Download PDF

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RU2350609C2
RU2350609C2 RU2004128393/04A RU2004128393A RU2350609C2 RU 2350609 C2 RU2350609 C2 RU 2350609C2 RU 2004128393/04 A RU2004128393/04 A RU 2004128393/04A RU 2004128393 A RU2004128393 A RU 2004128393A RU 2350609 C2 RU2350609 C2 RU 2350609C2
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Prior art keywords
phenyl
amino
benzofuran
alkyl
substituents
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RU2004128393/04A
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Russian (ru)
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RU2004128393A (en
Inventor
Ченгжи ЖАНГ (US)
Ченгжи ЖАНГ
Майкл БЕРК (US)
Майкл Берк
Жи ЧЕН (US)
Жи ЧЕН
Жак ДЮМА (US)
Жак Дюма
Донгпинг ФЭН (US)
Донгпинг ФЭН
Янмей ФЭН (US)
Янмей ФЭН
Холиа ХАТУМ-МОКДАД (US)
Холиа ХАТУМ-МОКДАД
Бенжамин Д. ДЖОНС (US)
Бенжамин Д. ДЖОНС
Гаэтан ЛАДУСЕР (US)
Гаэтан ЛАДУСЕР
Венди ЛИ (US)
Венди ЛИ
Бартон ФИЛЛИПС (US)
Бартон Филлипс
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БАЙЕР ХелсКер ЛЛСи
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Abstract

FIELD: chemistry; pharmacology. ^ SUBSTANCE: invention refers to new benzofuran and benzothiophen derivatives of general formula I, , wherein X is chosen from O and S; R1 is chosen from H, (C1-C6)alkyl, C(O)(C1-C6) alkyl and benzoyl; R2 is chosen from phenyl optionally substituted with 1 or 2 substitutes, each independently chosen from CN, NO2, (C1-C6)alkyl, (C1-C6)alkoxy, halogen, halogen(C1-C6)alkyl, pyridyl or benzo[1,3]dioxolyl optionally substituted with (C1-C6)alkyl. There are disclosed pharmaceutical composition based on compounds I and method of treatment. ^ EFFECT: compounds can be used to treat or prevent diseases associated with malignant cell proliferation. ^ 26 cl, 7 tbl, 365 ex

Description

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The text of the description is given in facsimile form.
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Claims (26)

1. Соединение формулы I
Figure 00000159

где X выбран из О и S;
R1 выбран из Н, (С1-С6)алкила, С(O)(С1-С6)алкила и бензоила;
R2 выбран из
фенила, необязательно замещенного 1 или 2 заместителями, каждый из которых независимо выбран из CN, NO2, (С1-С6)алкила, (С1-С6)алкокси, галогена, галоген(С1-С6)алкила,
пиридила или бензо[1,3]диоксолила, необязательно замещенных (С1-С6)алкилом,
R3 означает Н;
R4 выбран из пиперонила,
Y,
где Y означает морфолинил, пирролил, оксазолил, тиазолил, пиразолил, имидазолил, пиридинил, пирролидинил, имидазолидинил или тиофенил, необязательно замещенные 1, 2 или 3 заместителями, каждый из которых независимо выбран из
=O, галоген, NRBRB,
(С1-С6)алкокси,
С(O)RD, где RD выбран из RА,
(С1-С6)алкила,
фенила, необязательно замещенного 1, 2 или 3 заместителями, каждый из которых независимо выбран из
CN, NO2, галогена, галоген(С1-С6)алкила, галоген(С1-С6)алкокси, NRBRB, S(O)0-2RB, S(O)2NRBRB,
(С1-С6)алкокси, указанный алкокси необязательно содержит 1 или 2 заместителя, выбранные из ОН, NRBRB и (С1-С3)алкокси,
NRCRC, где RC выбран из RВ, C(O)RВ и S(O)2RB,
С(O)RD, где RD выбран из RA,
NRBRE, где RE выбран из C(O)RA, C(O)RB, S(O)2RB, S(O)2NRBRB, (С1-С6)алкила, и указанный алкил необязательно замещен CN, ОН, C(O)RА, NRВRВ;
RA в каждом случае независимо означает Н, (С1-С6)алкил и NRВRB;
RВ в каждом случае независимо означает Н или (С1-С6)алкил, и указанный алкил необязательно замещен ОН, галогеном, и где RB и RB вместе с атомом N, к которому они присоединены, могут образовать морфолинильный цикл или пиперазинильный цикл, который у имеющегося атома N необязательно содержит в качестве заместителя (С1-С6)алкил, и указанный алкил необязательно содержит в качестве заместителей ОН, =O, NH2, (С1-С6)алкокси, NH(С1-С3)алкил или N[(C1-С3)алкил]2;
R5 и R6 каждый означает Н;
или его фармацевтически приемлемая соль или сложный эфир.1. The compound of formula I
Figure 00000159

where X is selected from O and S;
R 1 is selected from H, (C 1 -C 6 ) alkyl, C (O) (C 1 -C 6 ) alkyl and benzoyl;
R 2 selected from
phenyl optionally substituted with 1 or 2 substituents, each independently selected from CN, NO 2 , (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy, halogen, halogen (C 1 -C 6 ) alkyl,
pyridyl or benzo [1,3] dioxolyl optionally substituted with (C 1 -C 6 ) alkyl,
R 3 means H;
R 4 selected from piperonyl,
Y
where Y is morpholinyl, pyrrolyl, oxazolyl, thiazolyl, pyrazolyl, imidazolyl, pyridinyl, pyrrolidinyl, imidazolidinyl or thiophenyl, optionally substituted with 1, 2 or 3 substituents, each of which is independently selected from
= O, halogen, NR B R B ,
(C 1 -C 6 ) alkoxy,
C (O) R D , where R D is selected from R A ,
(C 1 -C 6 ) alkyl,
phenyl optionally substituted with 1, 2 or 3 substituents, each of which is independently selected from
CN, NO 2 , halogen, halogen (C 1 -C 6 ) alkyl, halogen (C 1 -C 6 ) alkoxy, NR B R B , S (O) 0-2 R B , S (O) 2 NR B R B
(C 1 -C 6 ) alkoxy, said alkoxy optionally contains 1 or 2 substituents selected from OH, NR B R B and (C 1 -C 3 ) alkoxy,
NR C R C , where R C is selected from R B , C (O) R B and S (O) 2 R B ,
C (O) R D , where R D is selected from R A ,
NR B R E , where R E is selected from C (O) R A , C (O) R B , S (O) 2 R B , S (O) 2 NR B R B , (C 1 -C 6 ) alkyl and said alkyl is optionally substituted with CN, OH, C (O) R A , NR B R B ;
R A in each case independently means H, (C 1 -C 6 ) alkyl and NR B R B ;
R B in each case independently means H or (C 1 -C 6 ) alkyl, and said alkyl is optionally substituted with OH, halogen, and where R B and R B together with the N atom to which they are attached can form a morpholinyl ring or piperazinyl a ring which, optionally, on an existing N atom contains (C 1 -C 6 ) alkyl as a substituent, and said alkyl optionally contains OH, = O, NH 2 , (C 1 -C 6 ) alkoxy, NH (C 1 as substituents) -C 3 ) alkyl or N [(C 1 -C 3 ) alkyl] 2 ;
R 5 and R 6 each means H;
or a pharmaceutically acceptable salt or ester thereof. 2. Соединение по п.1, в котором Х означает О.2. The compound according to claim 1, in which X means O. 3. Соединение по п.1, в котором Х означает S.3. The compound according to claim 1, in which X means S. 4. Соединение по п.2, в котором R2 выбран из фенила, пиридила или бензо[1,3]диоксолила, каждый из которых необязательно содержит заместители.4. The compound according to claim 2, in which R 2 selected from phenyl, pyridyl or benzo [1,3] dioxolyl, each of which optionally contains substituents. 5. Соединение по п.2, в котором R4 выбран из Y и фенила, каждый из которых необязательно содержит заместители.5. The compound according to claim 2, in which R 4 selected from Y and phenyl, each of which optionally contains substituents. 6. Соединение по п.2, в котором R2 выбран из фенила, пиридила или бензо[1,3]диоксолила, каждый из которых необязательно содержит заместители, и R4 выбран из Y и фенила, каждый из которых необязательно содержит заместители.6. The compound according to claim 2, in which R 2 selected from phenyl, pyridyl or benzo [1,3] dioxolyl, each of which optionally contains substituents, and R 4 selected from Y and phenyl, each of which optionally contains substituents. 7. Соединение по п.5, в котором R4 выбран из фенила и Y, где Y выбран из пирролила, оксазолила, тиазолила, пиразолила, имидазолила, пирролидинила, имидазолидинила, тиофенила и пиридинила, и каждый циклический фрагмент необязательно содержит заместители.7. The compound according to claim 5, in which R 4 is selected from phenyl and Y, where Y is selected from pyrrolyl, oxazolyl, thiazolyl, pyrazolyl, imidazolyl, pyrrolidinyl, imidazolidinyl, thiophenyl and pyridinyl, and each cyclic fragment optionally contains substituents. 8. Соединение по п.6, в котором R2 и R4 каждый независимо необязательно замещены 1 или 2 заместителями, и R3, R5 и R6 означают Н.8. The compound according to claim 6, in which R 2 and R 4 each independently optionally substituted with 1 or 2 substituents, and R 3 , R 5 and R 6 mean N. 9. Соединение по п.8, в котором R1 выбран из Н и (С1-С6)алкила.9. The compound of claim 8, in which R 1 selected from H and (C 1 -C 6 ) alkyl. 10. Соединение по п.3, в котором R2 выбран из фенила, пиридила или бензо[1,3]диоксолила, каждый из которых необязательно содержит заместители.10. The compound according to claim 3, in which R 2 selected from phenyl, pyridyl or benzo [1,3] dioxolyl, each of which optionally contains substituents. 11. Соединение по п.3, в котором R4 выбран из Y и фенила, каждый из которых необязательно содержит заместители.11. The compound according to claim 3, in which R 4 selected from Y and phenyl, each of which optionally contains substituents. 12. Соединение по п.3, в котором R2 выбран из фенила, пиридила или бензо[1,3]диоксолила, каждый из которых необязательно содержит заместители, и R4 выбран из Y и фенила, каждый из которых необязательно содержит заместители.12. The compound according to claim 3, in which R 2 selected from phenyl, pyridyl or benzo [1,3] dioxolyl, each of which optionally contains substituents, and R 4 selected from Y and phenyl, each of which optionally contains substituents. 13. Соединение по п.11, в котором R4 выбран из фенила и Y, где Y выбран из пирролила, оксазолила, тиазолила, пиразолила, имидазолила, пирролидинила, имидазолидинила, тиофенила и пиридинила, и каждый циклический фрагмент необязательно содержит заместители.13. The compound of claim 11, wherein R 4 is selected from phenyl and Y, wherein Y is selected from pyrrolyl, oxazolyl, thiazolyl, pyrazolyl, imidazolyl, pyrrolidinyl, imidazolidinyl, thiophenyl and pyridinyl, and each cyclic moiety optionally contains substituents. 14. Соединение по п.12, в котором R2 и R4 каждый независимо необязательно замещены 1 или 2 заместителями, и R3, R5 и R6 означают Н.14. The compound of claim 12, wherein R 2 and R 4 are each independently optionally substituted with 1 or 2 substituents, and R 3 , R 5 and R 6 are N. 15. Соединение по п.14, в котором R1 выбран из Н и (С1-С6)алкила.15. The compound of claim 14, wherein R 1 is selected from H and (C 1 -C 6 ) alkyl. 16. Соединение, выбранное из группы, включающей (3-амино-6-фенилбензофуран-2-ил)-(2,4-дихлорфенил)-метанон, (3-амино-6-пиридин-3-илбензофуран-2-ил)-(2,4-дихлорфенил)-метанон, [3-амино-6-(3-нитрофенил)-бензофуран-2-ил]-(2,4-дихлорфенил)-метанон, [3-амино-6-(3-аминофенил)-бензофуран-2-ил]-(2,4-дихлорфенил)-метанон, 3-[3-амино-2-(2,4-дихлорбензоил)-бензофуран-6-ил]-бензонитрил, N-{3-[3-амино-2-(2,4-дихлорбензоил)-бензофуран-6-ил]-фенил}-метансульфонамид, N-{3-[3-амино-2-(2,4-дихлорбензоил)-бензофуран-6-ил]-фенил}-ацетамид, [3-амино-6-(2-метилпиридин-3-ил)-бензофуран-2-ил]-(2,4-дихлорфенил)-метанон, 5-[3-амино-2-(2,4-дихлорбензоил)-бензофуран-6-ил]-никотинамид, 3-[3-амино-2-(2,4-дихлорбензоил)-бензофуран-6-ил]-бензолсульфонамид, (3-амино-5-фтор-6-пиридин-3-илбензофуран-2-ил)-(2,4-дихлорфенил)-метанон, {3-амино-6-[3-((S)-2,3-дигидроксипропиламино)-фенил]-бензофуран-2-ил}-(2,4-дихлорфенил)-метанон, 3-[3-амино-2-(2,4-дихлорбензоил)-бензофуран-6-ил]-N-метилбензамид, [3-амино-6-(1-метил-1Н-имидазол-4-ил)-бензофуран-2-ил]-(2,4-дихлорфенил)-метанон, 3-[3-амино-2-(2-хлор-4-фтор-бензоил)-бензофуран-6-ил]-бензамид, 2-{3-[3-амино-2-(2,4-дихлорбензоил)-бензофуран-6-ил]-фенил}-ацетамид, [3-амино-6-(2-метилтиазол-4-ил)-бензофуран-2-ил]-(2,4-дихлорфенил)-метанон, N-{3-[3-амино-2-(2,4-дихлорбензоил)-бензофуран-6-ил]-бензил}-метансульфонамид, N-{3-[3-амино-2-(2,4-дихлорбензоил)-бензофуран-6-ил]-бензил}-ацетамид, [3-амино-6-(2-метилоксазол-4-ил)-бензофуран-2-ил]-(2-метоксифенил)-метанон, [3-амино-6-(3-фтор-5-нитрофенил)-бензофуран-2-ил]-(2,4-дихлорфенил)-метанон, [3-амино-6-(3-метансульфонилфенил)-бензофуран-2-ил]-(2,4-дихлорфенил)-метанон, [3-амино-6-(2-фтор-пиридин-3-ил)-бензофуран-2-ил]-(2,4-дихлорфенил)-метанон, и [3-амино-6-(2-метиламинопиридин-3-ил)-бензофуран-2-ил]-(2,4-дихлорфенил)-метанон.16. A compound selected from the group consisting of (3-amino-6-phenylbenzofuran-2-yl) - (2,4-dichlorophenyl) methanone, (3-amino-6-pyridin-3-ylbenzofuran-2-yl) - (2,4-dichlorophenyl) methanone, [3-amino-6- (3-nitrophenyl) benzofuran-2-yl] - (2,4-dichlorophenyl) methanone, [3-amino-6- (3 -aminophenyl) benzofuran-2-yl] - (2,4-dichlorophenyl) methanone, 3- [3-amino-2- (2,4-dichlorobenzoyl) benzofuran-6-yl] benzonitrile, N- { 3- [3-amino-2- (2,4-dichlorobenzoyl) benzofuran-6-yl] phenyl} methanesulfonamide, N- {3- [3-amino-2- (2,4-dichlorobenzoyl) benzofuran -6-yl] phenyl} -acetamide, [3-amino-6- (2-methylpyridin-3-yl) benzofuran-2-yl] - (2,4-dichlorophenyl) methanone, 5- [3-amino-2- (2,4-dichlorobenzoyl) benzofuran-6-yl] nicotinamide, 3- [3-amino-2- (2,4-dichlorobenzoyl) benzofuran-6-yl] benzene sulfonamide, (3-amino-5-fluoro-6-pyridin-3-ylbenzofuran-2-yl) - (2,4-dichlorophenyl) methanone, {3-amino-6- [3 - ((S) -2.3 -dihydroxypropylamino) phenyl] benzofuran-2-yl} - (2,4-dichlorophenyl) methanone, 3- [3-amino-2- (2,4-dichlorobenzoyl) benzofuran-6-yl] -N- methylbenzamide, [3-amino-6- (1-methyl-1H-imidazol-4-yl) benzofuran-2-yl] - (2,4-dichlorophenyl) methanone, 3- [3-amino-2- ( 2-chloro-4-fluoro-benzoyl) benzofuran-6-yl] benzamide, 2- {3- [3-amino-2- (2,4-dichlorobenzoyl) benzofuran-6-yl] phenyl} - acetamide, [3-amino-6- (2-methylthiazole- 4-yl) benzofuran-2-yl] - (2,4-dichlorophenyl) methanone, N- {3- [3-amino-2- (2,4-dichlorobenzoyl) benzofuran-6-yl] benzyl } -methanesulfonamide, N- {3- [3-amino-2- (2,4-dichlorobenzoyl) benzofuran-6-yl] benzyl} -acetamide, [3-amino-6- (2-methyloxazole-4- yl) -benzofuran-2-yl] - (2-methoxyphenyl) methanone, [3-amino-6- (3-fluoro-5-nitrophenyl) benzofuran-2-yl] - (2,4-dichlorophenyl) - methanone, [3-amino-6- (3-methanesulfonylphenyl) benzofuran-2-yl] - (2,4-dichlorophenyl) methanone, [3-amino-6- (2-fluoro-pyridin-3-yl) -benzofuran-2-yl] - (2,4-dichlorophenyl) -methanone, and [3-amino-6- (2-methylaminopyridin-3-yl) -benzofuran-2-yl] - (2,4-dichlorophenyl) methanone. 17. Фармацевтическая композиция, ингибирующая пролиферацию опухолевых клеток, включающая соединение формулы I по п.1.17. A pharmaceutical composition inhibiting the proliferation of tumor cells, comprising a compound of formula I according to claim 1. 18. Композиция по п.17, в которой Х означает О.18. The composition according to 17, in which X means O. 19. Композиция по п.17, в которой Х означает S.19. The composition according to 17, in which X means S. 20. Композиция по п.18, где R2 выбран из фенила, пиридила или бензо[1,3]диоксолила, каждый из которых необязательно содержит заместители, и R4 выбран из Y и фенила, каждый из которых необязательно содержит заместители.20. The composition according to p. 18, where R 2 selected from phenyl, pyridyl or benzo [1,3] dioxolyl, each of which optionally contains substituents, and R 4 selected from Y and phenyl, each of which optionally contains substituents. 21. Композиция по п.19, где R2 выбран из фенила, пиридила или бензо[1,3]диоксолила, каждый из которых необязательно содержит заместители, и R4 выбран из Y и фенила, каждый из которых необязательно содержит заместители.21. The composition according to claim 19, where R 2 selected from phenyl, pyridyl or benzo [1,3] dioxolyl, each of which optionally contains substituents, and R 4 selected from Y and phenyl, each of which optionally contains substituents. 22. Способ лечения или предотвращения заболеваний, связанных с пролиферацией опухолевых клеток, включающий введение нуждающемуся в нем пациенту эффективного количества соединения формулы I по п.1.22. A method of treating or preventing diseases associated with the proliferation of tumor cells, comprising administering to a patient in need thereof an effective amount of a compound of formula I according to claim 1. 23. Способ по п.22, в котором Х означает О.23. The method according to item 22, in which X means O. 24. Способ по п.22, в котором Х означает S.24. The method according to item 22, in which X means S. 25. Способ по п.23, где R2 выбран из фенила, пиридила или бензо[1,3]диоксолила, каждый из которых необязательно содержит заместители, и R4 выбран из Y и фенила, каждый из которых необязательно содержит заместители.25. The method according to item 23, where R 2 selected from phenyl, pyridyl or benzo [1,3] dioxolyl, each of which optionally contains substituents, and R 4 selected from Y and phenyl, each of which optionally contains substituents. 26. Способ по п.24, где R2 выбран из фенила, пиридила или бензо[1,3]диоксолила, каждый из которых необязательно содержит заместители, и R4 выбран из Y и фенила, каждый из которых необязательно содержит заместители. 26. The method according to paragraph 24, where R 2 selected from phenyl, pyridyl or benzo [1,3] dioxolyl, each of which optionally contains substituents, and R 4 selected from Y and phenyl, each of which optionally contains substituents.
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AU2003215380B2 (en) 2008-10-02
CN1639145A (en) 2005-07-13
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HRP20040874A2 (en) 2006-05-31
MXPA04007031A (en) 2004-10-11
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ATE338036T1 (en) 2006-09-15
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WO2003072566A1 (en) 2003-09-04
US7585888B2 (en) 2009-09-08
KR20040096600A (en) 2004-11-16
CA2474511A1 (en) 2003-09-04
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RU2004128393A (en) 2005-05-10
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PL373373A1 (en) 2005-08-22
CO5611124A2 (en) 2006-02-28
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AU2003213219A1 (en) 2003-09-09
US20050139814A1 (en) 2005-06-30
HK1080467B (en) 2008-02-01
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HK1080466A1 (en) 2006-04-28
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MA27111A1 (en) 2004-12-20
CN1639146A (en) 2005-07-13
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MXPA04007391A (en) 2004-10-11
CN1319961C (en) 2007-06-06
HUP0600156A2 (en) 2006-06-28
AU2003213219B2 (en) 2009-02-26
AU2003215380A1 (en) 2003-09-09
KR100965021B1 (en) 2010-06-21
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US20090054514A1 (en) 2009-02-26

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